A tandem approach to isoquinolines from 2-azido-3-arylacrylates and alpha-diazocarbonyl compounds

J Org Chem. 2008 May 16;73(10):3928-30. doi: 10.1021/jo8003259. Epub 2008 Apr 10.

Abstract

2-Azido-3-arylacrylates react with alpha-diazocarbonyl compounds and triphenylphosphine to furnish isoquinolines in 60-92% yields. The tandem process involves a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring closure. The procedure is efficient, rapid, and general, and the substrates are readily available.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemistry*
  • Diazonium Compounds / chemistry*
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Acrylates
  • Diazonium Compounds
  • Isoquinolines